Entrepreneur

Love of the Sea and Business

Richard O’Leary ’54 has a small painting among the mementos at his oceanside home in Ogunquit, Maine. It’s a small painting he made of a young boy watching a ship passing in the distance.

It harkens to O’Leary’s boyhood infatuation with the ocean, which led to a remarkable career, from service as a naval officer and merchant mariner to Commandant of the U.S. Merchant Marine Academy and founder and president of Cruise International / CI Travel, a company of 2,500 employees and a 14-ship fleet that cruised some of America’s most prominent harbors.

Watch an interview with O’Leary

“I grew up poor, the son of an Irish immigrant,” he says. “My love of the ocean and admiration for the people I knew from Maine Maritime led me to apply to the academy.” Even though the cost of attendance was modest, O’Leary worked for a year at a bakery (earning 62 cents an hour to start) to make his way into the school.

“One of the best things about MMA is it puts you into a well-defined field, especially for those in the maritime trades,” O’Leary says. “You can earn very good money, and there are a lot of exciting things to do. I sensed that, way back when I was a freshman, it would be a good thing for me.”

As a deck grad, he enjoyed his early years at sea, in particular as a deck officer aboard SS United States (the “Big U”), a passenger ship known for its record-speed crossing of the Atlantic, which he traversed 250 times. His management and business acumen began to emerge when he came ashore, first at Kings Point, and progressively until he founded Cruise International in 1972, a 34-year adventure that grew into a multi-million-dollar business, which he sold to his employees upon his retirement.

O’Leary’s business philosophy: “Try to do the very best you can, then let it go.

“Do more than people expect you to in life and business, because most people are trying to do less.

“With any success achieved, share it with two groups: the employees and the people who believed and invested in you.”

O’Leary, who was among the first inducted into MMA’s Hall of Fame and also awarded an honorary doctorate from the academy in 1998, has been generous in giving back. He has supported the college for many years with a substantial scholarship fund and a grant in his remainder trust.“I must say, the academy has managed it beautifully,” he says. “They’ve done that, and also found people who really needed the help. I remember how difficult it was for me. So, it’s been a great pleasure and makes me very proud.”

Photos: courtesy of Richard O’Leary & Billy Sims

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